Design and synthesis of a hybrid framework of indanone and chromane: Total synthesis of a homoisoflavanoid, brazilane

Jinwoo Kim; Ikyon Kim

doi:10.1039/c7ob02758c

Design and synthesis of a hybrid framework of indanone and chromane: Total synthesis of a homoisoflavanoid, brazilane

Jinwoo Kim, Ikyon Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane. Pd-catalyzed Suzuki-Miyaura cross-coupling of 4-chloro-2H-chromene-3-carbaldehydes with (hetero)aryl boronic acids was employed as a means to introduce a wide variety of (hetero)aryl groups as the D ring and intramolecular Friedel-Crafts acylation was utilized to construct the C ring of this skeleton. Total synthesis of the natural product, brazilane, was also demonstrated via this new chemical framework.

Original language	English
Pages (from-to)	89-100
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	1
DOIs	https://doi.org/10.1039/c7ob02758c
Publication status	Published - 2017

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2017R1A2A2A05069364).

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c7ob02758c

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abstract = "A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane. Pd-catalyzed Suzuki-Miyaura cross-coupling of 4-chloro-2H-chromene-3-carbaldehydes with (hetero)aryl boronic acids was employed as a means to introduce a wide variety of (hetero)aryl groups as the D ring and intramolecular Friedel-Crafts acylation was utilized to construct the C ring of this skeleton. Total synthesis of the natural product, brazilane, was also demonstrated via this new chemical framework.",

author = "Jinwoo Kim and Ikyon Kim",

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AU - Kim, Ikyon

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Design and synthesis of a hybrid framework of indanone and chromane: Total synthesis of a homoisoflavanoid, brazilane

Abstract

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